14770-96-8

Usage

Preparation

Preparation by Friedel–Crafts acylation of hydroquinone dimethyl ether with benzoyl chloride in the presence of aluminium chloride, in carbon disulfide first at 25° for 48 h, then at 50° for 30 min (55%) or at r.t. for 48 h (by-product).

InChI:InChI=1/C14H12O3/c1-17-11-7-8-13(15)12(9-11)14(16)10-5-3-2-4-6-10/h2-9,15H,1H3

Upstream product

• 4038-13-5 2,5-dimethoxybenzophenone 
• 98-88-4 benzoyl chloride 
• 150-78-7 1,4-dimethoxybezene 
• 1523-19-9 4-methoxyphenyl benzoate 
• 7446-70-0 aluminium trichloride 
• 672-13-9 2-hydroxy-5-methoxybenzaldehyde 
• 98-80-6 phenylboronic acid 
• 108-86-1 bromobenzene 
• 41951-80-8 2-(hydroxy(phenyl)methyl)-4-methoxyphenol 
• 5720-07-0 4-methoxyphenylboronic acid 
• 93021-93-3 1-methoxy-4-((3-phenylprop-2-yn-1-yl)oxy)benzene 
• 150-76-5 4-methoxy-phenol 
• 65-85-0 benzoic acid 
• 103702-18-7 5-methoxy-3-phenylbenzofuran-2(3H)-one 

Downstream Products

• 4038-13-5 2,5-dimethoxybenzophenone 
• 41951-80-8 2-(hydroxy(phenyl)methyl)-4-methoxyphenol 
• 36041-39-1 2-benzoyl-1,4-benzoquinone 
• 876487-03-5 2,6-Dibenzoyl-4-methoxy-phenol 
• 858854-47-4 1,3-dibenzoyl-2-benzoyloxy-5-methoxy-benzene 
• 1202186-04-6 1-(2-hydroxy-5-methoxyphenyl)-1-phenyl-4-methyl-4-(tetrahydropyran-2-yloxy)-pent-2-yn-1-ol 
• 40547-03-3 6-Methoxy-4-phenyl-2H-1-benzopyran-2-one 
• 1279130-96-9 (E)-4-methoxy-2-(phenyl((3,4,5-trimethoxyphenyl)imino)methyl)phenol 
• 1279131-19-9 (S)-4-methoxy-2-(phenyl((3,4,5-trimethoxyphenyl)amino)methyl)phenol 
• 1334247-38-9 (S)-2-(amino(phenyl)methyl)-4-methoxyphenol 
• 1334335-06-6 2-(imino(phenyl)methyl)-4-methoxyphenol 
• 93655-47-1 3-acetyl-6-methoxy-4-phenyl-2H-chromen-2-one 

Relevant academic research and scientific papers

Aerobic Copper-Catalyzed Salicylaldehydic Cformyl?H Arylations with Arylboronic Acids

We report a challenging copper-catalyzed Cformyl?H arylation of salicylaldehydes with arylboronic acids that involves unique salicylaldehydic copper species that differ from reported salicylaldehydic rhodacycles and palladacycles. This protocol has high chemoselectivity for the Cformyl?H bond compared to the phenolic O?H bond involving copper catalysis under high reaction temperatures. This approach is compatible with a wide range of salicylaldehyde and arylboronic acid substrates, including estrone and carbazole derivatives, which leads to the corresponding arylation products. Mechanistic studies show that the 2-hydroxy group of the salicylaldehyde substrate triggers the formation of salicylaldehydic copper complexes through a CuI/CuII/CuIII catalytic cycle.

Substituent and Surfactant Effects on the Photochemical Reaction of Some Aryl Benzoates in Micellar Green Environment?

In this study, we carried out preparative and mechanistic studies on the photochemical reaction of a series of p-substituted phenyl benzoates in confined and sustainable micellar environment. The aim of this work is mainly focused to show whether the nature of the surfactant (ionic or nonionic) leads to noticeable selectivity in the photoproduct formation and whether the electronic effects of the substituents affect the chemical yields and the rate of formation of the 5-substituted-2-hydroxybenzophenone derivatives. Application of the Hammett linear free energy relationship (LFER) on the rate of formation of benzophenone derivatives, on the lower energy band of the UV-visible absorption spectra of the aryl benzoates and 5-substituted-2-hydroxybenzophenone derivatives allows a satisfactory quantification of the substituent effects. Furthermore, UV-visible and 2D-NMR (NOESY) spectroscopies have been employed to measure the binding constant Kb and the location of the aryl benzoates within the hydrophobic core of the micelle. Finally, TD-DFT calculations have been carried out to estimate the energies of the absorption bands of p-substituted phenyl benzoates and 5-substituted-2-hydroxybenzophenone derivatives providing good linear correlation with those values measured experimentally.

Water-Tolerant ortho-Acylation of Phenols

A metal-free, water-tolerant, and one-pot process for ortho-acylation of phenols promoted by the iodine source/hydrogen peroxide system has been developed. This transformation undergoes ether formation, iodocyclization, C-C bond cleavage, and oxidative hydrolysis in a one-step manner, which is supported by control experiments.

Photo-Fries rearrangement in flow under aqueous micellar conditions

A flow edition of photo-Fries rearrangement for the synthesis of 2-acylphenols in an aqueous micellar medium has been described. We take advantage of a narrow channel reactor and micelle-induced confinement effect to refine both the efficiency and selectivity of the parent photoreaction. This journal is

Nickel-Catalyzed Decarbonyloxidation of 3-Aryl Benzofuran-2(3H)-ones to 2-Hydroxybenzophenones

We have developed a protocol to facilitate the nickel-catalyzed decarbonyloxidation of 3-aryl benzofuran-2(3H)-ones to 2-hydroxybenzophenones under mild conditions, which is an efficient approach for the decarbonyloxidation of lactones in organic synthesis. A diverse range of substrates can undergo C(O)-O/C(O)-C bond cleavage to generate the target products in good yields. These 2-hydroxybenzophenones can be converted into a variety of compounds via reactions such as esterification, cyclization, and reduction.

Selectivity in the photo-fries rearrangement of some aryl benzoates in green and sustainable media. Preparative and mechanistic studies

Irradiation of a series of p-substituted aryl benzoates under N2 atmosphere in homogeneous and micellar media was investigated by means of steady-state condition and of time-resolved spectroscopy. A notable selectivity in favor of the 2-hydroxybenzophenone derivatives was observed in micellar media. The benzophenone derivatives were the main photoproduct. On the other hand, in homogeneous media (cyclohexane, acetonitrile, and methanol) the observed product distribution was entirely different, viz. substituted 2-hydroxybenzophenones, p-substituted phenols, benzyl and benzoic acid were found. The binding constants in the surfactant were also measured and NOESY experiments showed that the aryl benzoates were located in the hydrophobic core of the micelle. Laser flash photolysis experiments led to the characterization of both p-substituted phenoxy radical and substituted 2-benzoylcyclohexadienone transients in homogeneous and micellar environment.

Intramolecular hydrogen-bond activation for the addition of nucleophilic imines: 2-hydroxybenzophenone as a chemical auxiliary

The addition of nucleophilic imines, using 2-hydroxybenzophenone as a chemical auxiliary, is presented. An intramolecular six-membered ring via hydrogen bonding that enhances the reactivity and selectivity is the key of this strategy, which is supported b

Acid-Functionalised Magnetic Ionic Liquid [AcMIm]FeCl4 as Catalyst for Oxidative Hydroxylation of Arylboronic Acids and Regioselective Friedel–Crafts Acylation

An acid-functionalised, magnetic, room-temperature ionic liquid, 1-acyl-3-methylimidazolium tetrachloroferrate ([AcMIm]FeCl4), was synthesised and its optical, magnetic, and thermal properties were investigated. The magnetic moment (0.05402 emu in 2 T magnetic fields) showed strong paramagnetic behaviour, and thermogravimetric analysis indicated very good thermal stability with a decomposition temperature higher than 230 °C. Additionally, [AcMIm]FeCl4 efficiently catalysed the oxidative ipso-hydroxylation of arylboronic acids and regioselective Friedel–Crafts acylation without external organic solvent or additives, such as acids, base, and ligands. This functionalised ionic liquid, [AcMIm]FeCl4, was recycled and reused at least six times without significant loss of its catalytic properties and stability.

Copper catalyzed oxidative deamination of Betti bases: An efficient approach for benzoylation/formylation of naphthols and phenols

An efficient route for benzoylation or formylation of naphthols/phenols is developed via oxidative deamination of Betti bases. A copper salt catalyst with TBHP as an oxidant is used. Water is used as a reagent as well as solvent. The reaction proceeds through a regioselective radical pathway. Most importantly, the position of acylation is unambiguous. The method is also applicable to non-hydroxy substrates.

Chemoselective C-benzoylation of phenols by using ALCl3under solvent-free conditions

Substituted phenols were chemo-selectively reacted with benzoylchloride in presence of aluminum chloride under solvent-free condition to afford the corresponding 2′-hydroxy aryl benzophenones in excellent yields (72-96%). Naphthol benzoylation resulted in lower yields as compared to phenols. Both reactions completed in 5-10 min with quantitative yields providing excellent control over regioselectivity of products.